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10-15 - Chapter 6 Nucleophilic Substitution Reactions...

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1 Nucleophilic Substitution Reactions Chapter 6 1 Chapter 6: Nucleophilic Substitution Reactions + C Cl HC C Cl + C C HC 2 H H H H Which reactant is the acid? A B Some Examples of Substitution Reactions + C Cl H H H Cl + C N H N H H 3 H H Which reactant is the base? A B Substitution Reactions Nu + C X C Nu X +   4 base acid acid base nucleophile electrophile substitution of a C-Nu bond for a C-X bond Thermodynamics vs Kinetics H H 5 H O + C Cl H H + Cl C HO H H acid base base acid nucleophile electrophile Equilibria Δ G° = Δ H° - T Δ 6 energy reaction Δ G ° H O + C Cl H H H + Cl C HO H H H
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2 Equilibria free energy enthalpy entropy Δ G° = Δ H° - T Δ 7 H O + C Cl H H H + Cl C HO H H H energy reaction Δ Equilibria 1. Cl - more stable than HO - (see pK a s). 2. C–O bond more stable than C–Cl bond. Factors favoring the products: 8 energy reaction Δ 330 kJ/mole 355 kJ/mole H O + C Cl H H H + Cl C HO H H H Δ G° = 100 kJ/mol Equilibria Δ G° = -RT ln K eq K eq = e Δ RT temperature ( K ) constant (0.00831 kJ/ K ) 9 H O + C Cl H H H + Cl C HO H H H energy reaction Δ if Δ G° = - 100 kJ/mole K eq = 3.4 x 10 17 at 298 ° K Rates H O C Cl H H H Δ G Transition state theory: Rate [t.s.] transition state = k [HO
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